BENZPHETAMINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C17H21N
Molecular Weight	239.3553
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

C[C@@H](CC1=CC=CC=C1)N(C)CC2=CC=CC=C2

InChI

InChIKey=YXKTVDFXDRQTKV-HNNXBMFYSA-N

InChI=1S/C17H21N/c1-15(13-16-9-5-3-6-10-16)18(2)14-17-11-7-4-8-12-17/h3-12,15H,13-14H2,1-2H3/t15-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C17H21N
Molecular Weight	239.3553
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

Benzphetamine is a sympathomimetic agent with properties similar to dextroamphetamine. It is used in the management of exogenous obesity as a short term (a few weeks) adjunct in a regimen of weight reduction based on caloric restriction in patients with an initial body mass index (BMI) of 30 kg/m2 or higher who have not responded to appropriate weight reducing regimen (diet and/or exercise) alone. Presumably, benzphetamine produces its effects through mechanisms similar to amphetamine via induces synaptic vesicular amine transporter, but precise mechanism of action of benzphetamine is not known.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Synaptic vesicular amine transporter 57	Activator 1,430

Conditions

Condition	Modality	Targets	Highest Phase	Product
Exogenous obesity 19	Palliative		Approved 8,429	BENZPHETAMINE HYDROCHLORIDE

AUC

Value	Dose	Co-administered	Analyte	Population
4.9 μg × min/mL	10 mg/kg 1 times / day multiple, intraperitoneal		BENZPHETAMINE plasma	Rattus norvegicus

F_unbound

Value	Dose	Co-administered	Analyte	Population
13%			BENZPHETAMINE unknown	Homo sapiens

Doses

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Dose	Population	Adverse events
80 mg 3 times / day multiple, oral (max)	unhealthy, 54 n = 20	Other AEs: Gastrointestinal signs and symptoms, Dizziness...

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AEs

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AE	Significance	Dose	Population
Appetite disorder	1 patient	80 mg 3 times / day multiple, oral (max)	unhealthy, 54 n = 20
Chest pain	1 patient	80 mg 3 times / day multiple, oral (max)	unhealthy, 54 n = 20
Fatigue	1 patient	80 mg 3 times / day multiple, oral (max)	unhealthy, 54 n = 20
Headache	1 patient	80 mg 3 times / day multiple, oral (max)	unhealthy, 54 n = 20
Malaise	1 patient	80 mg 3 times / day multiple, oral (max)	unhealthy, 54 n = 20

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,737		substrate 1,217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP450 65 CYP3A 191 CYP2B 10 CYP2B1 12

Drug as victim

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Target	Modality	Activity
CYP2B 10	substrate 3,367	yes
CYP2B1 12	substrate 3,367	yes
CYP2D6 1,217	substrate 3,367	yes
CYP3A 191	substrate 3,367	yes
CYP3A4 1,737	substrate 3,367	yes

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:3044	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3044
ChemicalBook	CB3705216	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB3705216
ZINC	ZINC000000968305	http://zinc15.docking.org/substances/ZINC000000968305

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PubMed

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Title	Date	PubMed
Characterization of rabbit liver P450IIE1 synthesized in transformed yeast cells.	1990 Oct	2292581
Essential requirements for substrate binding affinity and selectivity toward human CYP2 family enzymes.	2003 Jan 1	12464242
Resonance Raman studies of cytochrome P450 2B4 in its interactions with substrates and redox partners.	2008 Mar 25	18311926
Ligand diversity of human and chimpanzee CYP3A4: activation of human CYP3A4 by lithocholic acid results from positive selection.	2009 Jun	19299527

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Patents

Sample Use Guides

In Vivo Use Guide

Dosage should be individualized according to the response of the patient. The suggested dosage ranges from 25 to 50 mg one to three times daily. Treatment should begin with 25 to 50 mg once daily with subsequent increase in individual dose or frequency according to response. A single daily dose is preferably given in mid-morning or mid-afternoon, according to the patient's eating habits. In an occasional patient it may be desirable to avoid late afternoon administration. Use of benzphetamine hydrochloride is not recommended in individuals under 12 years of age.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical
Record UNII	0M3S43XK27
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BENZPHETAMINE

Common Name

English

(+)-BENZPHETAMINE

Common Name

English

BENZFETAMINE

Official Name

English

BENZPHETAMINE [VANDF]

Common Name

English

BENZPHETAMINE [MI]

Common Name

English

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Classification Tree

Code System

Code

Agent Affecting Nervous System

NCI_THESAURUS

C29728

Sec. 1308.11 Schedule III.

DEA NO.

1228

Appetite Alteration

NDF-RT

N0000175372

Sympathetic Activity Alteration

NDF-RT

N0000175651

Obesity

LIVERTOX

97

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Code System

Code

Type

Description

DRUG CENTRAL

329

PRIMARY

RXCUI

1422

PRIMARY

RxNorm

CHEBI

3044

PRIMARY

ChEMBL

CHEMBL3545985

PRIMARY

HSDB

3294

PRIMARY

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Related Record

Type

Details


					3T7136LE8K

ALPHA-1A ADRENERGIC RECEPTOR

TARGET -> AGONIST

Amount:


					43DWT87QT7

BENZPHETAMINE HYDROCHLORIDE

SALT/SOLVATE -> PARENT


					50U1BO5G5P

ALPHA-2A ADRENERGIC RECEPTOR

TARGET -> AGONIST

Amount:

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Related Record

Type

Details


					0M3S43XK27

BENZPHETAMINE

ACTIVE MOIETY

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SMILES

InChI

Approval Year

Targets

Conditions

AUC

Funbound

Doses

AEs

Overview

OverviewOther

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

F_unbound